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How do I hack Hotmail, AOL etc?

Subtitle: Wireless Oakland is piloting and I need to warn my users....

Since I use very few of the "free" email services, (Hotmail, AOL, etc.), Instant Messengers, (Yahoo, MSN etc.), I want to check my facts about the transmission forms of these systems which are the predominant vehicles of communication for many.

My questions are:-

1. Do any of the standard "free" email systems generally encrypt their transmissions "out of the box" of are they simply an HTTP transfer in clear text.

2. Which of the "free" email systems come "out of the box" with unencrypted logins?

3. Which of the "free" email systems allow you to "upgrade" to a secure login but then revert back to "in clear" HTTP?

4. Which of the "free" email systems allow you to switch everything to an encrypted connection for all transactions and remember it for every time you connect?

5. Can you answer the same questions for the common IM programs that everyone's kids use?

6. Can you list any other concerns regarding "in clear transmissions" over a public wireless network that the general users would fall foul of that will really scare the BeJabers out of them....

Don\'t SYN us.... We\'ll SYN you..... \"A nation that draws too broad a difference between its scholars and its warriors will have its thinking done by cowards, and its fighting done by fools.\" - Thucydides